DE3604781A1 - Novel silanes, their preparation, and insecticidal compositions containing these compounds - Google Patents
Novel silanes, their preparation, and insecticidal compositions containing these compoundsInfo
- Publication number
- DE3604781A1 DE3604781A1 DE19863604781 DE3604781A DE3604781A1 DE 3604781 A1 DE3604781 A1 DE 3604781A1 DE 19863604781 DE19863604781 DE 19863604781 DE 3604781 A DE3604781 A DE 3604781A DE 3604781 A1 DE3604781 A1 DE 3604781A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- alkyl
- halogen
- halo
- alkynyloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Abstract
Description
Die Erfindung betrifft neue Silane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende insektizide Mittel.The invention relates to new silanes, processes for their preparation and insecticidal agents containing these compounds.
Es ist bereits bekannt, daß bestimmte Silane insektizide Eigenschaften besitzen (JP-OS 1 23 491/85).It is already known that certain silanes have insecticidal properties own (JP-OS 1 23 491/85).
Aufgabe der vorliegenden Erfindung ist die Bereitstellung von neuen Verbindungen, die eine bessere insektizide Wirkung zeigen als die für diesen Zweck bereits bekannten Verbindungen.The object of the present invention is to provide new compounds that have better insecticidal activity than the compounds already known for this purpose.
Es wurde nun gefunden, daß Silane der allgemeinen Formel I
in der
R1 Aryl, durch C1-C4-Alkyl, Halogen-C1-C4-alkyl, Phenyl-
C1-C4-alkyl, C2-C4-Alkenyl, Halogen-C2-C4-alkenyl,
Phenyl-C2-C4-alkenyl, C2-C4-Alkinyl, Halogen-C2-C4-
alkinyl, Phenyl-C2-C4-alkinyl, C1-C4-Alkoxy, Halogen-
C1-C4-alkoxy, Phenyl-C1-C4-alkoxy, C2-C4-Alkenyloxy,
Halogen-C2-C4-alkenyloxy, Phenyl-C2-C4-alkenyloxy,
C2-C4-Alkinyloxy, Halogen-C2-C4-alkinyloxy, Phenyl-
C2-C4-alkinyloxy, Alkylsulfonyloxy, Halogenalkylsulfonyloxy,
Arylsulfonyloxy, Halogen, Cyan, Nitro,
Aryloxy, Halogenaryloxy, C1-C4-Alkyl-aryloxy oder
Nitroaryloxy substituiertes Aryl und
R2 Phenyl, Pyridyl oder durch C1-C6-Alkyl, Halogen-C1-C6-
alkyl, Phenyl-C1-C6-alkyl, durch O-, N- oder S-Atome
unterbrochenes C1-C6-Alkyl, C2-C4-Alkenyl, Halogen-
C2-C4-alkenyl, Phenyl-C2-C4-alkenyl, C1-C4-Alkoxy,
Halogen-C1-C4-alkoxy, Phenyl-C1-C4-alkoxy, C2-C4-
Alkenyloxy, Halogen-C2-C4-alkenyloxy, Phenyl-C2-C4-
alkenyloxy, C2-C4-Alkinyloxy, Halogen-C2-C4-alkinyloxy,
Phenyl-C2-C4-alkinyloxy, Aryloxy, Halogenaryloxy,
C1-C4-Alkylaryloxy, Arylamino, Halogenarylamino, C1-C4-
Alkylarylamino, Aryl-N-C1-C4-alkyl-amino, Aryl-N-C1-C4-
acyl-amino, Aroyl, Halogenaroyl, C1-C4-Alkylaroyl, Aryl,
Halogenaryl, C1-C4-Alkylaryl oder durch Halogen ein-
oder mehrfach substituiertes Phenyl oder Pyridyl
bedeuten, eine bessere Wirkung gegen Insekten besitzen als
bereits bekannte, strukturverwandte Verbindungen.It has now been found that silanes of the general formula I in the
R 1 aryl, by C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl, C 2 -C 4 alkenyl, halo-C 2 -C 4 alkenyl , Phenyl-C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halogen-C 2 -C 4 -alkynyl, phenyl-C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen-C 1 -C 4 alkoxy, phenyl-C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, halogen-C 2 -C 4 alkenyloxy, phenyl-C 2 -C 4 alkenyloxy, C 2 -C 4 -Alkynyloxy, halo-C 2 -C 4 -alkynyloxy, phenyl- C 2 -C 4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halogen, cyano, nitro, aryloxy, haloaryloxy, C 1 -C 4 -alkyl-aryloxy or nitroaryloxy substituted aryl and
R 2 is phenyl, pyridyl or C 1 -C 6 alkyl, halo-C 1 -C 6 - alkyl, phenyl-C 1 -C 6 alkyl, by O, N or S atoms which is interrupted C 1 -C 6- alkyl, C 2 -C 4 -alkenyl, halogen-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy, halogen-C 1 -C 4 -alkoxy, Phenyl-C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, halogen-C 2 -C 4 -alkenyloxy, phenyl-C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, halogen-C 2 -C 4 alkynyloxy, phenyl-C 2 -C 4 alkynyloxy, aryloxy, haloaryloxy, C 1 -C 4 -Alkylaryloxy, arylamino, haloarylamino, C 1 -C 4 - alkylarylamino, aryl-NC 1 -C 4 alkyl amino, aryl-NC 1 -C 4 -acylamino, aroyl, haloaroyl, C 1 -C 4 alkylaroyl, aryl, haloaryl, C 1 -C 4 alkylaryl or phenyl or pyridyl which is mono- or polysubstituted by halogen
mean have a better action against insects than already known, structurally related compounds.
Überraschenderweise wurden hier neue Wirkstoffe gefunden, die gegen wichtige Schädlinge, wie zum Beispiel Plutella xylostella oder Spodoptera littoralis, wirksam sind.Surprisingly, new active ingredients were found here that against important pests, such as Plutella xylostella or Spodoptera littoralis, are effective.
Der in der allgemeinen Formel I als R1 bezeichnete Arylrest umfaßt die Reste Phenyl, 1-Naphthyl, 2-Naphthyl, Benzofuran- 5-yl, Benzothiophen-5-yl, Benzofuran-6-yl, Benzothiophen-6-yl, Benzoxazol-5-yl, Benzoxazol-6-yl, Indan-5-yl, Indan-6-yl, 1,4- Benzodioxan-6-yl, 1,3-Benzodioxan-6-yl, 1,3-Benzodioxan-7-yl und 1,3-Benzodioxol-5-yl.The aryl radical designated R 1 in the general formula I comprises the radicals phenyl, 1-naphthyl, 2-naphthyl, benzofuran-5-yl, benzothiophene-5-yl, benzofuran-6-yl, benzothiophene-6-yl, benzoxazole 5-yl, benzoxazol-6-yl, indan-5-yl, indan-6-yl, 1,4-benzodioxan-6-yl, 1,3-benzodioxan-6-yl, 1,3-benzodioxan-7- yl and 1,3-benzodioxol-5-yl.
Von den erfindungsgemäßen Verbindungen zeichnen sich durch ihre
insektizide Wirkung insbesondere diejenigen aus, bei denen in
der allgemeinen Formel I
R1 Chlorphenyl, Bromphenyl, Fluorphenyl, Methylphenyl, Methoxyphenyl,
Ethoxyphenyl, Difluormethoxyphenyl, Fluorethoxyphenyl, Trifluorethoxyphenyl und
R2 Phenoxyphenyl, Fluor-phenoxyphenyl oder Phenoxypyridyl
darstellen.
Of the compounds according to the invention are notable for their insecticidal activity, in particular those in which in the general formula I
R 1 chlorophenyl, bromophenyl, fluorophenyl, methylphenyl, methoxyphenyl, ethoxyphenyl, difluoromethoxyphenyl, fluoroethoxyphenyl, trifluoroethoxyphenyl and
R 2 phenoxyphenyl, fluorophenoxyphenyl or phenoxypyridyl
represent.
Die erfindungsgemäßen Silane lassen sich zum Beispiel herstellen, indem man Dimethyldichlorsilan der Formel II zuerst mit einer Grignardverbindung der allgemeinen Formel IIIThe silanes according to the invention can be prepared, for example, by dimethyldichlorosilane of the formula II first with a Grignard compound of the general formula III
R1MgX (III)R 1 MgX (III)
zu einer Zwischenverbindung der allgemeinen Formel IV und diese anschließend mit einer Grignardverbindung der allgemeinen Formel Vto an intermediate compound of the general formula IV and then with a Grignard compound of the general formula V
XMgCH2CH2CH2R2 (V)XMgCH 2 CH 2 CH 2 R 2 (V)
zu dem gewünschten Verfahrensprodukt umsetzt, wobei R1 und R2 die oben genannte Bedeutung haben und X Halogen bedeutet.converted to the desired process product, wherein R 1 and R 2 have the meaning given above and X is halogen.
Besonders vorteilhaft ist es, beide Reaktionsschritte in einer Eintopfreaktion durchzuführen.It is particularly advantageous to have both reaction steps in one Carry out a one-pot reaction.
Als Lösungsmittel eignen sich gegenüber den Reaktanden, insbesondere den Grignardreagenzien, inerte Stoffe, wie aliphatische und aromatische Kohlenwasserstoffe, wie zum Beispiel Hexan, Benzol oder Toluol, und Ether, wie zum Beispiel Diethylether, Tetrahydrofuran oder Dimethoxyethan.Suitable solvents for the reactants are, in particular the Grignard reagents, inert substances such as aliphatic and aromatic hydrocarbons such as Hexane, benzene or toluene, and ethers, such as diethyl ether, Tetrahydrofuran or dimethoxyethane.
Die Durchführung der Reaktionen erfolgt bei Temperaturen zwischen -78° und 140°C, vorzugsweise bei 20-80°C, in der Regel bei Normaldruck. The reactions are carried out at temperatures between -78 ° and 140 ° C, preferably at 20-80 ° C, in the Usually at normal pressure.
Die nach oben genannten Verfahren hergestellten erfindungsgemäßen Verbindungen können nach den üblichen Verfahren aus dem Reaktionsgemisch isoliert werden, beispielsweise durch Abdestillieren des eingesetzten Lösungsmittels bei normalem oder vermindertem Druck oder durch Extraktion.The inventive methods produced by the above-mentioned methods Compounds can be obtained from the Reaction mixture are isolated, for example by distillation of the solvent used with normal or reduced Pressure or by extraction.
Ein erhöhter Reinheitsgrad kann in der Regel durch säulenchromatographische Aufreinigung sowie durch fraktionierte Destillation erhalten werden.An increased degree of purity can usually be determined by column chromatography Purification as well as by fractional Distillation can be obtained.
Die erfindungsgemäßen Verbindungen sind in der Regel farblose Öle, die in praktisch allen organischen Lösungsmitteln gut, in Wasser dagegen schwer löslich sind.The compounds according to the invention are generally colorless Oils that are good in virtually all organic solvents, are, however, poorly soluble in water.
Die Anwendung der erfindungsgemäßen Verbindungen kann in Konzentrationen von 0,0005 bis 5,0%, vorzugsweise von 0,001 bis 0,1% erfolgen, worunter das Gewicht in Gramm Wirkstoff in 100 ml Zubereitung zu verstehen ist.The compounds according to the invention can be used in concentrations from 0.0005 to 5.0%, preferably from 0.001 to 0.1%, including the weight in grams of active ingredient in 100 ml preparation is to be understood.
Die erfindungsgemäßen Verbindungen können entweder allein, in Mischung miteinander oder mit anderen insektiziden Wirkstoffen angewendet werden. Gegebenenfalls können auch andere Pflanzenschutz- oder Schädlingsbekämpfungsmittel, wie zum Beispiel Insektizide, Akarizide oder Fungizide, je nach dem gewünschten Zweck zugesetzt werden.The compounds of the invention can either be used alone, in a mixture with one another or with other insecticidal active ingredients be applied. If necessary, others can Plant protection or pesticides, such as Example insecticides, acaricides or fungicides, depending on the desired Purpose to be added.
Eine Förderung der Wirkintensität und der Wirkungsgeschwindigkeit kann zum Beispiel durch wirkungssteigernde Zusätze, wie organische Lösungsmittel, Netzmittel und Öle erzielt werden. Solche Zusätze lassen daher gegebenenfalls eine Verringerung der Wirkstoffdosierung zu. A promotion of the intensity and speed of action can, for example, by additions such as organic solvents, wetting agents and oils can be achieved. Such additives may therefore cause a reduction the drug dosage.
Als Mischungspartner können außerdem Phospholipide verwendet werden, zum Beispiel solche aus der Gruppe Phosphatidylcholin, den hydrierten Phosphatidylcholinen, Phosphatidylethanolamin, den N-Acyl-phosphatidylethanolaminen, Phosphatidylinosit, Phosphatidylserin, Lysolecithin und Phosphatidylglycerol.Phospholipids can also be used as mixing partners such as those from the group phosphatidylcholine, the hydrogenated phosphatidylcholines, phosphatidylethanolamine, the N-acyl-phosphatidylethanolamines, phosphatidylinositol, Phosphatidylserine, lysolecithin and phosphatidylglycerol.
Zweckmäßig werden die gekennzeichneten Wirkstoffe oder deren Mischungen in Form von Zubereitungen wie Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägerstoffen beziehungsweise Verdünnungsmitteln und gegebenenfalls Haft-, Netz-, Emulgier- und/oder Dispergierhilfsmitteln angewandt.The labeled active ingredients or their Mixtures in the form of preparations such as powders, spreading agents, Granules, solutions, emulsions or suspensions, with addition of liquid and / or solid carriers respectively Diluents and, if necessary, adhesives, wetting agents, emulsifiers and / or dispersing aids applied.
Geeignete flüssige Trägerstoffe sind zum Beispiel aliphatische und aromatische Kohlenwasserstoffe wie Benzol, Toluol, Xylol, Cyclohexanon, Isophoron, Dimethylsulfoxid, Dimethylformamid, weiterhin Mineralölfraktionen und Pflanzenöle.Suitable liquid carriers are, for example, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, Cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, still mineral oil fractions and vegetable oils.
Als feste Trägerstoffe eignen sich Mineralien, zum Beispiel Bentonit, Silicagel, Talkum, Kaolin, Attapulgit, Kalkstein und pflanzliche Produkte, zum Beispiel Mehle.Minerals are suitable as solid carriers, for example Bentonite, silica gel, talc, kaolin, attapulgite, limestone and herbal products, for example flour.
An oberflächenaktiven Stoffen sind zu nennen zum Beispiel Calciumligninsulfonat, Polyethylenalkylphenylether, Naphthalinsulfonsäuren und deren Salze, Phenolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate sowie substituierte Benzolsulfonsäuren und deren Salze.Examples of surface-active substances are: Calcium lignin sulfonate, polyethylene alkylphenyl ether, naphthalene sulfonic acids and their salts, phenolsulfonic acids and their salts, Formaldehyde condensates, fatty alcohol sulfates and substituted Benzenesulfonic acids and their salts.
Der Anteil des bzw. der Wirkstoffe(s) in den verschiedenen Zubereitungen kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 10 bis 90 Gewichtsprozent Wirkstoff, etwa 90 bis 10 Gewichtsprozent flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Gewichtsprozent oberflächenaktive Stoffe. The proportion of the active ingredient (s) in the different preparations can vary widely. For example the agents contain about 10 to 90 percent by weight of active ingredient, about 90 to 10 weight percent liquid or solid carriers and optionally up to 20 percent by weight of surface-active Fabrics.
Die Ausbringung der Mittel kann in üblicher Weise erfolgen, zum Beispiel mit Wasser als Träger in Spritzbrühmengen von etwa 100 bis 3000 Liter/Hektar. Eine Anwendung der Mittel im sogenannten Low-Volume und Ultra-Low-Volume-Verfahren ist ebenso möglich wie ihre Applikation in Form von sogenannten Mikrogranulaten.The funds can be distributed in the usual way to Example with water as a carrier in spray liquor quantities of about 100 up to 3000 liters / hectare. An application of the means in the so-called Low-volume and ultra-low-volume processes are also possible like their application in the form of so-called microgranules.
Die Herstellung dieser Zubereitungen kann in an sich bekannter Art und Weise, zum Beispiel durch Mahl- oder Mischverfahren, durchgeführt werden. Gewünschtenfalls können Zubereitungen der Einzelkomponenten auch erst kurz vor ihrer Verwendung gemischt werden, wie es zum Beispiel im sogenannten Tankmixverfahren in der Praxis durchgeführt wird.The preparation of these preparations can be done in a manner known per se Way, for example by grinding or mixing processes, be performed. If desired, preparations of the Individual components are only mixed shortly before they are used be used, for example in the so-called tank mix process in in practice.
Zur Herstellung der Zubereitungen werden zum Beispiel die folgenden Bestandteile eingesetzt:For the preparation of the preparations, for example following components:
-
a) 80 Gewichtsprozent Wirkstoff
15 Gewichtsprozent Kaolin
5 Gewichtsprozent oberflächenaktive Stoffe auf Basis des Natriumsalzes des N-Methyl-N- oleyl-taurins und des Calciumsalzes der Ligninsulfonsäurea) 80 percent by weight of active ingredient
15% by weight kaolin
5 percent by weight of surface-active substances based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulfonic acid -
b) 45 Gewichtsprozent Wirkstoff
5 Gewichtsprozent Natriumaluminiumsilikat
15 Gewichtsprozent Cetylpolyglycolether mit 8 Mol Ethylenoxid
2 Gewichtsprozent Spindelöl
10 Gewichtsprozent Polyethylenglycol
23 Gewichtsprozent Wasser b) 45 percent by weight of active ingredient
5% by weight sodium aluminum silicate
15 percent by weight cetyl polyglycol ether with 8 moles of ethylene oxide
2% by weight spindle oil
10% by weight polyethylene glycol
23 weight percent water -
c) 20 Gewichtsprozent Wirkstoff
35 Gewichtsprozent Bentonit
8 Gewichtsprozent Zellpech
2 Gewichtsprozent Natriumsalz des N-Methyl-N-oleyl-taurins
35 Gewichtsprozent Kieselsäurec) 20 percent by weight of active ingredient
35 percent by weight bentonite
8% by weight cell pitch
2 percent by weight sodium salt of N-methyl-N-oleyl-taurine
35 weight percent silica -
d) 20 Gewichtsprozent Wirkstoff
75 Gewichtsprozent Isophoron
5 Gewichtsprozent Kombinationsemulgator aus Calciumdodecylbenzolsulfonat und Fettalkoholpolyglycoletherd) 20 percent by weight of active ingredient
75 weight percent isophorone
5% by weight combination emulsifier from calcium dodecylbenzenesulfonate and fatty alcohol polyglycol ether
Das nachfolgende Beispiel erläutert die Herstellung der erfindungsgemäßen Verbindungen. The following example explains the production of the invention Links.
Zu 2,4 ml (0,02 mol) Dichlordimethylsilan in 50 ml absolutem
Tetrahydrofuran wird bei Raumtemperatur eine Grignardlösung,
hergestellt aus 3,85 g (0,02 mol) 4-Bromchlorbenzol und 0,49 g
(0,02 mol) Magnesium in 20 ml Tetrahydrofuran, getropft und
eine Stunde bei Raumtemperatur nachgerührt. Anschließend wird
eine zweite Grignardlösung, bereitet aus 5,82 g (0,02 mol)
3-(3-Phenoxyphenyl)-propylbromid und 0,49 g (0,02 mol) Magnesium
in 20 ml Tetrahydrofuran, zugetropft. Nach vierstündigem
Erhitzen unter Rückfluß wird auf Ammoniumchloridlösung gegeben,
mit Ether extrahiert, mit Wasser gewaschen, über Magnesiumsulfat
getrocknet und eingeengt. Nach Chromatographie mit Hexan
an Kieselgel verbleiben 3,4 g an Produkt (= 46% der Theorie).
n: 1,5775A Grignard solution, prepared from 3.85 g (0.02 mol) of 4-bromochlorobenzene and 0.49 g (0.02 mol) of magnesium, is added to 2.4 ml (0.02 mol) of dichlorodimethylsilane in 50 ml of absolute tetrahydrofuran at room temperature in 20 ml of tetrahydrofuran, added dropwise and the mixture was stirred at room temperature for one hour. A second Grignard solution, prepared from 5.82 g (0.02 mol) of 3- (3-phenoxyphenyl) propyl bromide and 0.49 g (0.02 mol) of magnesium in 20 ml of tetrahydrofuran, is then added dropwise. After refluxing for four hours, the mixture is poured onto ammonium chloride solution, extracted with ether, washed with water, dried over magnesium sulfate and concentrated. After chromatography with hexane on silica gel, 3.4 g of product remain (= 46% of theory).
n : 1.5775
In analoger Weise wurden die folgenden Verbindungen hergestellt: The following compounds were prepared in an analogous manner:
Die folgenden Anwendungsbeispiele dienen zur Erläuterung der Anwendungsmöglichkeiten der erfindungsgemäßen Verbindungen, die in Form ihrer Zubereitungen erfolgte: The following application examples serve to explain the Possible uses of the compounds according to the invention, which took the form of their preparations:
Die erfindungsgemäßen Verbindungen wurden als wäßrige Emulsionen mit der Wirkstoffkonzentration 0,1% eingesetzt. Mit diesen Wirkstoffzubereitungen wurden Blumenkohlblättchen (Brassica oleracea var. botrytis) in Polystyrol-Petrischalen dosiert (4 mg Spritzbrühe/ cm2) gespritzt. Nach dem Antrocknen der Spritzbeläge wurden in jede Petrischale 10 Jungraupen der Kohlschabe (Plutella xylostella) eingezählt und für zwei Tage in den geschlossenen Petrischalen dem behandelten Futter exponiert. Kriterium für die Wirkungsbeurteilung war die Sterblichkeit der Raupen in % nach 2 Tagen.The compounds according to the invention were used as aqueous emulsions with an active ingredient concentration of 0.1%. With these active ingredient preparations, cauliflower leaves (Brassica oleracea var. Botrytis) were dosed into polystyrene petri dishes (4 mg spray liquor / cm 2 ). After the spray coatings had dried on, 10 young caterpillars of the cockroach (Plutella xylostella) were counted into each Petri dish and exposed to the treated feed in the closed Petri dishes for two days. Criterion for the effectiveness assessment was the mortality of the caterpillars in% after 2 days.
Im beschriebenen Versuch erzielten die Verbindungen gemäß den Herstellungsbeispielen 1 bis 6 eine hundertprozentige Mortalitätswirkung. In the experiment described, the connections achieved according to Production Examples 1 to 6 a 100% mortality effect.
Die erfindungsgemäßen Verbindungen wurden als wäßrige Emulsionen mit der Wirkstoffkonzentration 0,1% eingesetzt. Mit diesen Wirkstoffzubereitungen wurden je ein Fliederblattpaar der Puffbohne (Vicia faba) sowie 10 Larven (L 2) des Ägyptischen Baumwollwurmes (Spodoptera littoralis) pro Versuchsglied mit 4 mg Spritzbrühe/cm2 in Polystyrol-Petrischalen dosiert gespritzt. Die geschlossenen Petrischalen wurden dann im Labor unter Langtagbedingungen für zwei Tage aufgestellt. Kriterium für die Wirkungsbeurteilung war die Mortalität der Larven in % nach zwei Tagen.The compounds according to the invention were used as aqueous emulsions with an active ingredient concentration of 0.1%. With these active substance preparations, a pair of lilac leaves of the broad bean (Vicia faba) and 10 larvae (L 2) of the Egyptian cotton worm (Spodoptera littoralis) per test element were sprayed with 4 mg spray liquor / cm 2 into polystyrene petri dishes. The closed petri dishes were then set up in the laboratory under long day conditions for two days. The criterion for the effectiveness assessment was the mortality of the larvae in% after two days.
Im beschriebenen Versuch erbrachten die Verbindungen gemäß den Herstellungsbeispielen 1 bis 6 eine hundertprozentige Mortalität.In the experiment described, the connections were made according to the manufacturing examples 1 to 6 a hundred percent Mortality.
Claims (6)
R1 Aryl, durch C1-C4-Alkyl, Halogen-C1-C4-alkyl, Phenyl- C1-C4-alkyl, C2-C4-Alkenyl, Halogen-C2-C4-alkenyl, Phenyl-C2-C4-alkenyl, C2-C4-Alkinyl, Halogen-C2-C4- alkinyl, Phenyl-C2-C4-alkinyl, C1-C4-Alkoxy, Halogen- C1-C4-alkoxy, Phenyl-C1-C4-alkoxy, C2-C4-Alkenyloxy, Halogen-C2-C4-alkenyloxy, Phenyl-C2-C4-alkenyloxy, C2-C4-Alkinyloxy, Halogen-C2-C4-alkinyloxy, Phenyl- C2-C4-alkinyloxy, Alkylsulfonyloxy, Halogenalkylsulfonyloxy, Arylsulfonyloxy, Halogen, Cyan, Nitro, Aryloxy, Halogenaryloxy, C1-C4-Alkyl-aryloxy oder Nitroaryloxy substituiertes Aryl und
R2 Phenyl, Pyridyl oder durch C1-C6-Alkyl, Halogen-C1-C6- alkyl, Phenyl-C1-C6-alkyl, durch O-, N- oder S-Atome unterbrochenes C1-C6-Alkyl, C2-C4-Alkenyl, Halogen- C2-C4-alkenyl, Phenyl-C2-C4-alkenyl, C1-C4-Alkoxy, Halogen-C1-C4-alkoxy, Phenyl-C1-C4-alkoxy, C2-C4- Alkenyloxy, Halogen-C2-C4-alkenyloxy, Phenyl-C2-C4- alkenyloxy, C2-C4-Alkinyloxy, Halogen-C2-C4-alkinyloxy, Phenyl-C2-C4-alkinyloxy, Aryloxy, Halogenaryloxy, C1-C4-Alkylaryloxy, Arylamino, Halogenarylamino, C1-C4- Alkylarylamino, Aryl-N-C1-C4-alkyl-amino, Aryl-N-C1-C4- acyl-amino, Aroyl, Halogenaroyl, C1-C4-Alkylaroyl, Aryl, Halogenaryl, C1-C4-Alkylaryl oder durch Halogen ein- oder mehrfach substituiertes Phenyl oder Pyridyl
bedeuten. 1. Silanes of the general formula I in the
R 1 aryl, by C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, phenyl-C 1 -C 4 alkyl, C 2 -C 4 alkenyl, halo-C 2 -C 4 alkenyl , Phenyl-C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, halogen-C 2 -C 4 -alkynyl, phenyl-C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, halogen-C 1 -C 4 alkoxy, phenyl-C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, halogen-C 2 -C 4 alkenyloxy, phenyl-C 2 -C 4 alkenyloxy, C 2 -C 4 -Alkynyloxy, halo-C 2 -C 4 -alkynyloxy, phenyl- C 2 -C 4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halogen, cyano, nitro, aryloxy, haloaryloxy, C 1 -C 4 -alkyl-aryloxy or nitroaryloxy substituted aryl and
R 2 is phenyl, pyridyl or C 1 -C 6 alkyl, halo-C 1 -C 6 - alkyl, phenyl-C 1 -C 6 alkyl, by O, N or S atoms which is interrupted C 1 -C 6- alkyl, C 2 -C 4 -alkenyl, halogen-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy, halogen-C 1 -C 4 -alkoxy, Phenyl-C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, halogen-C 2 -C 4 -alkenyloxy, phenyl-C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, halogen-C 2 -C 4 alkynyloxy, phenyl-C 2 -C 4 alkynyloxy, aryloxy, haloaryloxy, C 1 -C 4 -Alkylaryloxy, arylamino, haloarylamino, C 1 -C 4 - alkylarylamino, aryl-NC 1 to C 4 alkyl amino, aryl-NC 1 -C 4 -acylamino, aroyl, haloaroyl, C 1 -C 4 alkylaroyl, aryl, haloaryl, C 1 -C 4 alkylaryl or phenyl or pyridyl which is mono- or polysubstituted by halogen
mean.
R1 Chlorphenyl, Bromphenyl, Fluorphenyl, Methylphenyl, Methoxyphenyl, Ethoxyphenyl, Difluormethoxyphenyl, Fluorethoxyphenyl, Trifluorethoxyphenyl und
R2 Phenoxyphenyl, Fluor-phenoxyphenyl oder Phenoxypyridyl darstellen.2. Silanes according to claim 1, wherein
R 1 chlorophenyl, bromophenyl, fluorophenyl, methylphenyl, methoxyphenyl, ethoxyphenyl, difluoromethoxyphenyl, fluoroethoxyphenyl, trifluoroethoxyphenyl and
R 2 represent phenoxyphenyl, fluorophenoxyphenyl or phenoxypyridyl.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DE19863604781 DE3604781A1 (en) | 1986-02-13 | 1986-02-13 | Novel silanes, their preparation, and insecticidal compositions containing these compounds |
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DE19863604781 DE3604781A1 (en) | 1986-02-13 | 1986-02-13 | Novel silanes, their preparation, and insecticidal compositions containing these compounds |
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DE3604781A1 true DE3604781A1 (en) | 1987-08-27 |
Family
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DE19863604781 Withdrawn DE3604781A1 (en) | 1986-02-13 | 1986-02-13 | Novel silanes, their preparation, and insecticidal compositions containing these compounds |
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